Dialkylamino-alkylethers of alkylolphenols



Patented Apr. 15, 1930' UNITED STATES PATENT OFFICE HANS HAHL, OF ELZBERFELD, GERMANY, ASSIGNOR TO WIN'I'HROP CHEMICAL COM- PANY, INQ, OF NEW YORK, N, Y.

DIALKYL AMINO-ALKYLETHEBS OF ALKYLOLPHENOLS No Drawing. Application filed July 18, 1927. Serial No. 206,793, and in Germany July 29, 1926.

The present invention relates to new dialkylamino-alkylethers of alkylolphenols, more particularly to new compounds of the general formula:

wherein one y stands for an alkylol group, for instance: GH OH or CH CH OH, the others for hydrogen, alkyl, alkylol or unsaturated aliphatic residues such as CH.CH=CH R for an alkylene radicle, R and R for alkyl .radicles containing less than three carbon atoms each.

These new compounds may be obtained for instance by causing basic alkylhalogenides to act upon phenols containing at least one alkylol group in the presence of an alkaline reacting agent as for instance sodium alcoholate.

These compounds possess valuable physiological properties, showing for instance strong anaesthetic action and being of relatively low toxicity. The aqueous solutions do not cause any irritating action. They are generally weakly colored and viscous oils, easily soluble in acids.

The following examples will illustrate my invention, all'parts being by weight Emample 1.20 parts of the sodium salt of eugenol methylol (Ber. d. Deutschen Chemis- 'chen Gesellschaft, vol. 35, page 3846) are heated for some time with 20 parts of diethylaminoethylchloride. When the reaction is complete, water is added, the separated oil removed and distilled. Under a pressure of 12 mm. at 213 to 215 C. a weakly yellow colored oil passes over and gives a crystalline salt with hydrochloric acid. The base has the following constitution H.CH==CH:

Example 2.-3.7 parts of sodium are dissolyed' in 50 parts of alcohol. 20 parts of sallgenin' and 30 parts of diethylaminoisobutylchloride of the formula:

can

are added and the whole is heated for 5 hours.

When the reaction is complete, the mass is poured into water. The oil which separates is removed, dried and distilled. Under a pressure of 15 mm. at 201 to 209 C. a yellow liquid passes over. The base has the following constitution 01H: .omomrK I claim c 1. As new products the compounds of the general formula:

wherein one y stands foran alkylol group, the other ys for hydrogen, alkyl, alkylol or unwherein one 3 CH OH, the others for hydrogen, alkyl,

saturated aliphatic residues, R for an alkylene radic1e,R and R for alkyl radicles containing less than 3 carbon atoms each.

2. As new products the compounds of the general formula:

. general formula;

wherein one 3 stands for an alkylol-group, the others for hydrogen, alkyl, alkylol or unsaturated aliphatic residues and R for an alkylene radicle containing at least two but not more than 4 carbon atoms each, which are yellow colored liquids easily soluble in acids, possessing valuable physiological properties.

4. As new products the compounds of the general formula:

in, 0.0mm: .NQ

stands for the group alkylol or unsaturated aliphatic residues, which are yellow colored liquids easily soluble in acids, possessing valuable physiological properties.

5. As new products the compounds having the general formula:

1 wherein 0: stands for a methoxy or methylolgroup and y for hydrogen, alkyl, alkylol or unsaturated aliphatic residues, which are yellow colored liquids easily soluble in acids possessing valuable physiological properties.

6. As a new product the compound of the formula:

(11H; .CH|.CH1.N

being a yellow oil distilling under a pressure of 12 mm. at 213218 C., being easily soluble in water and possessing valuable physiological properties.

In testimony whereof I have hereunto set my hand.

HAN S HAHL. 

